• Leadership Turnover: Five months into my tenure, 85% of the C-suite was replaced, shifting product goals and budgets.
• Inexperienced Teams: Product managers were promoted internally and lacked training in Agile methodologies and modern product management practices.
• Integration Challenges: Assurances of interoperability were overstated, with APIs bolted on rather than foundational, creating significant technical debt.
• Regulatory Complexity: U.S. federal regulatory changes, the first since 1961, were implemented inconsistently across 50 states, slowing development.
• Diverse Development Practices: Companies ranged from annual waterfall releases to daily Agile deployments, with one firm years behind schedule on its first online product.
• Cultural Resistance: Long-time employees resented the loss of autonomy and customer relationships, creating friction during the integration process.
• COVID-19 Impact: Remote work and travel restrictions hindered collaboration and team-building efforts.

APPROACH

To address these challenges, I focused on ...:

1. Defining a Unified Vision: Communicated the company’s vision of integrated product suites and emphasized the benefits of collaboration over autonomy.
2. Prioritizing High-Value Outcomes: Developed a framework to identify and prioritize initiatives based on metrics critical to the business, such as ARR growth, customer retention, and regulatory compliance.
3. Assessing and Building Talent: Evaluated existing product managers, hired for gaps in Agile expertise, market readiness, and product operations, and mentored teams to align with modern product management practices.
4. Standardizing Processes: Established consistent OKRs, KPIs, and Agile practices, including two-week sprints, retrospectives, and cross-team guilds to foster collaboration.
5. Addressing Technical Debt: Partnered with architects and developers to create foundational APIs and reduce technical debt, enabling smoother integrations and third-party compatibility.

EXECUTION

I led the team through ...:

1. Team Leadership: Interviewed all product managers to assess capabilities, hired new PMs for key gaps, and served as acting Chief Product Officer for four months during a medical vacancy.
2. Portfolio Alignment: Mapped functional overlaps across 16 products, prioritized integrations, and established a unified roadmap that rolled up into portfolio-level planning and tracking.
3. Process Standardization: Implemented consistent Agile practices across teams, reinstated retrospectives, and introduced Product Board software to centralize data and streamline portfolio management.
4. Regulatory Compliance: Advised on a flexible regulatory framework that accelerated delivery velocity tenfold, reducing timelines from months to weeks.
5. Customer-Centric Innovation: Led the development of a touchless COVID ID-check kiosk for high-traffic venues, balancing regulatory compliance and customer needs (see separate case study).
6. Stakeholder Communication: Delivered regular progress reports to the C-suite and PE board, ensuring alignment with North Star objectives and maintaining transparency.

The vision was steadily achieved following priority framework. The "Sheldon" COVID kiosk was delivered (see separate case study) while new and updated products were continously delivered.

RESULTS

1. Revenue Growth: Portfolio repricing increased ARR by 35%, driven by improved product value and customer retention.
2. Operational Efficiency: Standardized processes and reduced technical debt enabled faster delivery of new and updated products, improving customer satisfaction and reducing support incidents.
3. Team Development: Mentored product managers to adopt modern practices, fostering a culture of collaboration and continuous improvement.
4. Regulatory Success: Accelerated compliance with complex U.S. and international regulations, ensuring timely delivery of integrated solutions.
5. Customer Impact: Established consistent feedback channels with sales, customer success, and SMEs, uncovering and addressing customer needs early and often.
6. Strategic Alignment: Unified the product portfolio under a shared vision, increasing the company’s market value and positioning it for future sale.

We overcame numerous misunderstandings, cultural issues, and technological gaps to deliver better products with increased sales and customer retention, driving up the potential market value of the company at time of future sale.

LESSONS and TAKEAWAYS

1. Product Management as a Central Pillar: This experience reinforced the critical role of product management in aligning customer needs, business goals, and engineering capabilities to drive success.
2. Measuring What Matters: OKRs and KPIs provided clear visibility into progress toward key business objectives, ensuring focus on the metrics that mattered most.
3. Cultural Integration is Key: Overcoming resistance required consistent communication, empathy, and a clear articulation of the benefits of collaboration.
4. Preparation is Crucial: Inadequate assessments of acquired companies before the merger led to unforeseen challenges, highlighting the importance of thorough due diligence.